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Dr. Amy Wood

Psychologist Amy Wood helps adults to articulate and accomplish their own unique versions of success through psychotherapy, coaching, training, speaking, and writing. A pragmatic optimist, she is known for her capacity to simplify complexity and see manageable solutions amid the overwhelm of modern life and work. Dr. Wood is the author of the award-winning book Life Your Way: Refresh Your Approach to Success and Breathe Easier in a Fast-paced World and member of the National Speakers Association. She earned her doctorate from the Adler School of Professional Psychology, graduated from the College of Executive Coaching, and is a certified mediator. Visit her website at Connect with her on LinkedIn and find her on Facebook

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Posted: February 3, 2015

“We need to talk.” How to handle a difficult conversation

Written by: Dr. Amy Wood

My job involves a lot of listening and talking (in that order) and so it goes that a topic of conversation I get in a lot is, well, just that — conversation. Conversation is important in forging connections, processing emotions, figuring out solutions, but there’s an unfortunate lack of real live conversation in a world that increasingly seems to value technological transactions over face- to-face discourse. And we need conversation when misunderstandings and other interpersonal obstacles arise.

That last one, those “we need to talk” conversations, is what comes up most. How to summon the courage to speak honestly from the heart. How to confront another person without hurting feelings. How to approach delicate matters without causing anger or shame.

Just last week I was conversing about, you got it, conversation, with my colleague David Lee, a consultant known for helping business professionals have productive exchanges about challenging issues.  We agreed that the hardest part of those “we need to talk” conversations is getting started.

Approaching another person about a tense topic is never simple, and David suggests we can ease the process considerably by keeping these three ice-breaking pointers in mind:

Make it your problem even when it isn’t

David says that many of his clients, accomplished professionals who strive for fulfilling relationships at home and work, put off difficult conversations because they’re fed up with having to accept responsibility for problems they haven’t caused. Why, they lament, should they have to take on the task of addressing yet another person’s poor performance; shouldn’t the onus be on the misbehaving person to step up to the plate for a change?

David points out that not all of us are evolved enough to recognize when a “we need to talk” talk is in order, and even less of us are equipped with the social repertoire to open up the floor for a candid chat. If you’re interpersonally adept, then why not exercise your social strength by getting the ball rolling? Instead of feeling resentful, appreciate that social sensitivity is your specialty and take the lead. By demonstrating the importance of getting a difficult conversation going, you can be a role model for others who aren’t similarly gifted.

Prepare properly

David finds that people generally dread difficult conversations because past experience – breaking up with someone really needy who didn’t see it coming, firing a well-intentioned assistant who just couldn’t cut it – dictates that such encounters will be highly stressful. Most of us head into a “we need to talk” talk with a sense of let’s-get-this-over-with resignation, because we’re tired of ruminating about the predicament and just want it extinguished.

Difficult conversations go better when they are entered from a positive, hopeful and thoughtful perspective. So get your heart and head in the right place by calming down and getting centered before you open your mouth. Appropriate prepping involves talking through the issue with someone objective so that you can get fear, anger and other unproductive emotions out of the way, envisioning a positive outcome for all, and having faith that the other person will handle it okay.

Go for it like you’re Katie Couric (or Matt Lauer)

David has learned that difficult conversations are most likely to succeed when approached from the stance of a top notch interviewer, whose goal is always to bring out the best in those they are interviewing – because if you don’t bring out the best, you just get shut down, right? Great interviews don’t happen when you judge, criticize or intimidate. Similarly, “we need to talk” one-to-ones don’t take off when you even subtly accuse, demand, berate or threaten.

If  you want a touchy discussion to go somewhere, make your top priority to encourage confidence and comfort in the other person by gently asking to understand before you ask to be understood. When you embrace others with curiosity and respect – what we all want, regardless of our differences – you are most likely to overcome conflict and gain cooperation.

To carry a difficult conversation like a pro, David recommends that you ask these questions of yourself first:

  1. How would someone you respect for their wisdom, courage, emotional intelligence and compassion deal with this?”
  2. “What response (or action) on my part is for the greater good?
  3. Would the way I am thinking of bringing up this issue make the other person feel safe or threatened?”
  4. The way I’m thinking of dealing with this, would I be proud if some person I have huge respect for were there watching me?
  5. With whom might I talk through my viewpoint and the approach I’m considering, so I can get a third-party perspective?”

As a caveat, David warns that some difficult conversations will go up in flames no matter what you do.  The more you practice, however, the easier it becomes to say what’s hard to say.

David Lee is the founder and principal of HumanNature@work and the creator of Stories That Change. He’s an internationally recognized authority on organizational and managerial practices that optimize employee performance, morale, and engagement. He is also the author of “Managing Employee Stress and Safety,” as well over 60 articles and book chapters. You can download his articles at HumanNature@work, contact him at, or follow him on Twitter at

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